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Synlett 1999; 1999(S1): 881-884
DOI: 10.1055/s-1999-3100
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The Sakurai Reaction of 4-Acetoxycyclopentenone - Synthesis of trans-3-Allyl-4-vinylcyclopentanone

V. Helbling* , M. K. Eberle, R. Keese
  • *Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland; Fax +41(31)6 31 34 23; E-mail: reinhart.keese@ioc.unibe.ch
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Publication Date:
31 December 1999 (online)

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The Sakurai reaction of 4-acetoxycyclopentenone 1a leads to the aldol 2 and the bicyclic product 3. Retroaldol reaction leads to 4-allylcyclopentenone 7, from which the title compounds 9 was prepared in 28% overall yield. Further transformations of 3 are reported.

allyltrimethylsilane - 4-acetoxycyclopentenone - aldol products - 5-trimethylsilyl-bicyclo[3.3.0]octan-1-one - stereoelectronic control